10 Holiday Date Ideas

by Brett on December 6, 2010 · 61 comments

in Dating, Marriage, Relationships & Family

Not to toot my own horn, but I think I’m pretty good at a lot of relationship stuff. According to Kate, I’m very supportive, respectful, and trustworthy, am able to be the rock in a crisis, and have achieved the tricky balance between being nice and being a wiener.  But, as Kate can also attest, I struggle with a few things, and one of them is being romantic. I find it difficult to turn my thoughts and good intentions into spontaneous acts of affection.

Which is why I love the holidays.

This time of year takes all the work out of creating romance; the elements for it are already in place. We’re naturally feeling less guarded and cynical and are primed for bonding and cozy intimacy. Christmas lights and decorations set the scene and provide the requisite warm fuzzies. There’s magic in the air before you even lift a finger. The holidays are like a pool teeming with fish; all you have to do is let down your net to pick up a great bounty. The romantic atmosphere is out there; you simply need to take advantage of it. Here are 10 ways to do just that.

Looking at Christmas Lights

The warm twinkle of Christmas lights can set the heart of your special someone aglow and give you both the childlike feeling of magical possibilities. Ordinary houses and trees are transformed into something extraordinary.

Most towns have hot spots for Christmas light decorations. Some neighborhoods compete in an annual arms race to see which house can create the best display. Their neighborly pride is your gain. After you map out your route, create a holiday music mix that you can listen to while you’re driving around. You can never go wrong with classic Christmas crooners like Bing Crosby, Johnny Mathis, and Frank Sinatra.

Also be sure to check out the massive displays that are sometimes put on in parks by community organizations, where you can walk around in a winter wonderland of millions of lights. Check your local papers and ask your friends and co-workers to find out where they are. And try to go during the week as they can be especially packed on the weekends.

The final touch to this night of romantic holiday lights is a thermos full of thick, delicious hot chocolate.  Sip on it while you take in all the wonder. Your date’s heart will melt.

Holiday Baking

Man, I love Christmas cookies. Both the eating and making of them, and chances are your wife or girlfriend does too. Holiday baking is a fantastic date idea because it gives you a chance to work with your gal on a shared task, which in turns strengthens your bond and connection with her. And most importantly, you get a delicious treat to eat when you’re done!

To keep this date simple, stick with making one kind of cookie; I would vote for gingerbread men as wielding the cookie cutters and decorating the little guys is an enjoyable task. Invite your gal over (or go over her place=-she probably has the cookie cutters), turn on the holiday tunes, and start whipping up a batch. The oven won’t be the only thing warming up.

When you’re done baking, sit back and enjoy the fruits of your labor or make a plate and deliver them to a little old lady.

Ice Skating

Re-create the romantic ice-skating scene between Cary Grant and Loretta Young in The Bishop’s Wife by taking your gal to a skating rink. Between the hand holding and the full body embraces needed to keep each other from “accidentally” falling, you’ll have plenty of opportunities to strengthen the physical and emotional bond with your date. Many cities-even relatively balmy ones-have outdoor skating rinks during the winter that play Christmas music while you glide through the winter air. If yours does, take advantage of it while you can. It’s way more romantic than an indoor rink.

Decorate the Christmas Tree

A Christmas tree will infuse your date with the sights, lights, and smell of Christmas. It’s a holiday date trifecta. Start the date off by taking your special someone to a tree farm to pick out your tree. When you get home with your tree, play some Bing Crosby, sip some eggnog, and start decorating. If you’re hanging childhood ornaments, share some of the memories you have them with your date. She’ll think you’re sweet. You can even do some flirty teasing by putting tinsel on her head when she isn’t looking.

When you’re done decorating, turn off the lights in the house and show her you’re not afraid to have fun like a kid by lying side by side together under the Christmas tree and gazing up through the branches. Romantic smooching is 100% guaranteed.


During the holidays, the need for volunteers goes up substantially at food banks, soup kitchens, and clothing donation centers. They need more hands to handle the flood of donations that come in during this time of year. I know sorting cans of pumpkin doesn’t sound very romantic, but volunteering is a fantastic date idea, especially if you’re trying to figure out if she’s the one. You’ll get a chance to see your girlfriend in a different light. How does she treat others less fortunate than her? With compassion? Scorn? Does she whine when given an undesirable assignment or does she roll up her sleeves and get to work?

I definitely recommend doing the volunteering date after you’ve been with someone for awhile. It’s a little heavy for a first go round.

Christmas Movie Night

Instead of dropping a double sawbuck on taking your date out to the movies, stay in and watch some classic Christmas flicks together. Stock up on your favorite Christmas movies, make some hot cider, and curl up next to each other under a blanket for hours of holiday-themed viewing. Need some help on which Christmas movies to watch? Here’s a list of some of my favorites. Many of them happen to be romantic comedies. Bonus!

  • It’s a Wonderful Life
  • Holiday Inn
  • White Christmas
  • Miracle on 34th Street
  • The Bishop’s Wife
  • Elf
  • Peanut’s Christmas
  • A Christmas Story

Christmas Shopping

I know. I know. Consumerism has been sucking the life and spirit out of the holidays for decades, but it’s okay to take a sabbatical from the high horse and enjoy giving and receiving a few gifts this time of year. When it’s not overdone, it’s really a terrific tradition, no? I personally quite enjoy Christmas shopping. Buying gifts for loved ones amidst the hustle and bustle, festive store displays, and Christmas music gets me right into the holiday spirit. I’ve been doing more online shopping these days, and while it’s convenient, it’s just not the same.

Both you and your main squeeze probably have some shopping to do, so why not do it together? You can help each other pick gifts out for friends and family while taking in all the sights and sounds of the holidays. And of course you can drop hints about what you’d like to get from her by pointing out things that catch your eye. End the date by going home, ordering take out, and wrapping the presents together.

Go see The Nutcracker or A Christmas Carol

If your lady is into ballet, take her to a performance of The Nutcracker. Yeah, it’s ballet, but it’s a) romantic and b) a holiday tradition, which makes it perfect for this list. I always thought the sword fighting rats were pretty cool as a kid and that crazy guy with an eye patch was bad-a.

Going to see A Christmas Carol also makes for a terrific date. Every time I see it, I leave with an uplifted heart and a ton of holiday cheer. Here in Oklahoma, a local theater does A Christmas Carol with an Okie twist. Instead of taking place in Victorian England, the play is set in Territorial Oklahoma right after the Land Run. Scrooge is some sort of cattle and oil baron and instead of plum pudding the characters eat corn bread. It’s a kitschy good time.

Holiday Bed and Breakfast

This is a tradition my wife and I began while I was in law school. After the craziness of finals was over, we’d rent a room at a bed and breakfast near Oklahoma City for a night of romance and reconnecting. The bed and breakfast we go to is old and homey, and the charm is only heightened by the seasonal decorations. It’s a night of total relaxation. We’ll light a fire, watch some Christmas movies, and, well, you know.

In the morning, we’re treated to a holiday-themed breakfast of pumpkin spice pancakes and hot chocolate. After our little holiday getaway at the bed and breakfast, my wife and I always feel reconnected and filled with the holiday spirit.


Emotionally charged moments between you and your lady friend create memories and increase bonding. The adrenaline rush from speeding down a snowy hill can jump start your relationship. When the first snow covers the ground, grab your gal and your sled, find a quality hill, and take her for the ride of her life (for those of you in warmer climes, there’s always ice blocking!). Finish the date by warming up next to a fire. Oh yeah.

Do you have any other holiday date ideas? Share them with us in the comments!

{ 61 comments… read them below or add one }

1 Sasha @ Global Table Adventure December 6, 2010 at 9:30 pm

Nice list – I’m a huge fan of the movie “It’s a Wonderful Life.”
I agree with any outdoors activity – like sledding. A nice hike to a romantic vantage point is fun too… just bring hot cocoa in a thermos … or soup.

2 David Weiser December 6, 2010 at 9:41 pm

You missed the best Christmas movie of all (my wife’s favorite). Die Hard.

3 Brian December 6, 2010 at 9:46 pm

Great list! I would only add snuggling by the fireside, and in addition to hot chocolate there are plenty of holiday-inspired tea flavors out there to shake things up with the beverages.

4 Judson R. December 6, 2010 at 9:59 pm

Great article, Brett! One thing I’ve always enjoyed (alone or with company) is taking a late night walk through the snowy neighborhood. Nice to think by yourself, or just have a great (mostly quiet) moment with the one you love.

By the way- “…Balance between being nice and being a wiener” made me laugh for some reason. Thanks again, and merry Christmas.

5 Jacob December 6, 2010 at 10:08 pm

You could take your girl on a romantic horseback ride while smoking a pipe.

6 Brian M. December 6, 2010 at 10:11 pm

Sleigh ride in an Austrian sleigh.

7 Josh Knowles December 6, 2010 at 10:19 pm

I really appreciate that many of these ideas would cost little or nothing.

8 Kyle E December 6, 2010 at 10:28 pm

Great list! Also thought the Christmas movie list was good.
As always… excellent article.

9 Jeff December 6, 2010 at 10:35 pm

This post is a winner.

10 Anna December 6, 2010 at 10:39 pm

How about going to Handel’s “Messiah” as a sing-along? It’s really fun :)

11 cwflatt December 6, 2010 at 10:48 pm

David you already added our favorite Christmas movie along with “The Christmas Story” but a little known one to watch is called “The Ref” with Dennis Leary.

12 Will December 6, 2010 at 11:13 pm

Which bed in breakfast near OKC do you frequent? I’ve got a buddy who lives up there that I’d like to pass the info on to for him and his wife. Thanks!

13 Shawn December 6, 2010 at 11:41 pm

Another one that I thought was pretty good was “8 crazy nights”, and I’m not even Jewish

14 David December 7, 2010 at 12:29 am

Now the ground is white
So go it while you’re young
Take the girl tonight
And sign this sleighing-song

15 JG December 7, 2010 at 12:30 am

National Lampoon’s Christmas Vacation

’nuff said.

16 Daniel December 7, 2010 at 12:34 am

You forgot one of my favorite Christmas movies! What happened to “Die Hard” ?!?

17 Brett McKay December 7, 2010 at 2:33 am


It’s the Arcadian Inn in Edmond, OK. I highly recommend it for a romantic getaway:


18 Sandy December 7, 2010 at 4:34 am

I’ve found that my girlfriend really enjoys making a gingerbread house- we also like to set up a massive train around the entire living room that looks like its running through the snow.

19 Holiday Cheer December 7, 2010 at 4:36 am

I’m not into it, but my girl is a sucker for shopping for diamond jewelry. just shopping- not necessarily buying. She LOVES it.

20 Sam December 7, 2010 at 4:36 am

Adorable article!

21 Seth Ballard December 7, 2010 at 5:46 am

A carriage or sleigh ride is always a winner. Very classic.

22 Ryan Tyler December 7, 2010 at 6:53 am

My wife and I went shopping for sweaters the other night and stopped for some chicken wings after. It was a nice evening. If we would have went during the day, in the middle of the holiday rush, I’m not so sure that we would have had a great evening. Plan well, gentlemen.

23 Seth Ballard December 7, 2010 at 8:10 am

I wasn’t sure where to put this but I wanted to let the men out there know about the new Groupon Deal for today, 12/07/2010 only, in the Lakeland section. It is $20 for $40 Worth of Men’s Grooming Products from Lucky Tiger! I know you have mentioned these products so I wanted everyone to get a chance to get them cheaper. I am sure they will be on more in the future but you never know.

http://www.groupon.com/r/uu3115812 and then go to Lakeland for the deal! Trying not to spam you all but this is to good to pass up for our manly products!

24 Steve Miller December 7, 2010 at 8:29 am

My wife often talks about her favorite date: I told her to dress to warm and to meet me at a nearby park. When she got there, I took her on a short hike through the the snowy woods to a clearing where I pulled out a tarp to sit on and a small backpacking stove. We made hot chocolate and watched the snowfall for as long as we could keep warm.

25 Tracy Nash December 7, 2010 at 8:32 am

What, no “Bad Santa?” :-) Seriously though, great list, and lots of great suggestions in the comments. I agree with cwflatt, “The Ref” is hilarious, and “Die Hard” is an excellent choice if your date isn’t into the mushy stuff.

26 John Wright December 7, 2010 at 8:35 am

Similar to your post on Nutcracker and A Christmas Carol, I would suggest Handel’s Messiah or Amahl and the Night Visitors if you’re into Christmas Holiday classics (by classics I mean musical).

27 Steven Masters December 7, 2010 at 9:13 am

I find it hard to believe as awesome and manly as you are that you would have the same difficulty as I, but if Kate said it, I’ll have to believe it.
“But, as Kate can also attest, I struggle with a few things, and one of them is being romantic. I find it difficult to turn my thoughts and good intentions into spontaneous acts of affection.”
It’s nice to know I’m not alone in this department.

28 Adam R December 7, 2010 at 9:34 am

I LOVE that fact that you put volunteer on the list. I would put that as the #1 thing to do anytime, but especially during the holidays when the giving seems to increase (hence the need for help as well). It is an amazing feeling walking away from somewhere, knowing that you just finished loving on some random people, then being able to share in that feeling with your significant other.

Great Call!

29 Peter Zefo December 7, 2010 at 9:48 am

If you live in the Atlanta area, Shakespeare’s Tavern does a fantastic production of A Christmas Carol. While you’re there, try the Cornish Pasty or Shepherd’s Pie with a nice ale from Sweetwater Brewery.

30 Mary December 7, 2010 at 10:07 am

I agree with the above comment: Die Hard! Christmas Movie to not miss!

31 J D Armstrong December 7, 2010 at 10:59 am

Great list! I have already checked a few off of the list for this season but now have some good ideas for more!

One of my favorite parts of decorating the tree is going and cutting the tree. I have made it a tradition the past 3 years of going to a national forest and hunting for and cutting a tree (check your local area for permits and fees). There is something manly and satisfying about cutting down a tree and dragging it through knee deep snow! Also seems to impress the girlfriend in some heroic manner of conquering nature.

32 CoffeeZombie December 7, 2010 at 11:06 am

I haven’t been to Shakespeare Tavern’s Christmas Carol performance, but I can highly recommend it in general. Where else can you eat dinner while watching live performances (but don’t get too rowdy, or the actors *will* call you out). ;-)

33 Nick December 7, 2010 at 11:42 am

There are some incredibly romantic and hysterical Christmas movies that you left off your list.

Remember the Night (1940) – a perennial in our house; one of the great romantic movies.
It Happened on Fifth Avenue (194?)
The Cheaters (1949)
The Man Who Came to Dinner (1942)
Holiday (1937)

People oughta broaden their horizons. No need to visit that Red Rider BB gun if you’ve already witnessed it hundreds of times.

34 Steve Cianca December 7, 2010 at 11:42 am

Good post Brett. I liked the link to the “Nice Guys Don’t Have to Finish Last” (that was quite the educational piece). I, too, am not spontaneously romantic, but this list gives me some good (and inexpensive!) ideas for treating my wife of 23 years to a fun night out during the holidays. It’s a little trickier when you have kids–as you now will learn over the next 18 years! Merry Christmas and Happy New Year!

35 Ryan December 7, 2010 at 12:41 pm

Most major cities will have a park that has lights set up in them. Often times they’ll have a horse drawn carriage, which has been a major win for me in the past

36 Bill December 7, 2010 at 2:42 pm

Admire the intent, but this entire list seems unbelievably saccharine. Also somewhat disconcerting that a grown man, creator of a fine modern manliness webmagazine, feels he must euphemize the implied sexual act into the phrase “well, you know.”

37 William Tinsley December 7, 2010 at 3:53 pm

I can’t believe that you left out Christmas Vacation on the movie list!

38 Mitch Somerville December 7, 2010 at 4:08 pm

Brett, you left out the greatest Christmas movie of all time:

Die Hard

Addmitedly the manly amongst us may like it more than our ladies, but I watch it every Christmas without fail. And for those of you with any doubt that its a Christmas movie may I direct you to its soundtrack: Winter Wonderland, Christmas in Hollis, Let it Snow, Let it Snow, Let it Snow, Ode to Joy, Jingle Bells. That’s a Christmas movie soundtrack if ever there was one.

One of my favorite romantic holiday activities would have to be the winter walk. Going for a stroll over snow covered lanes has always had a romantic feel for me.

39 MMA Girl December 7, 2010 at 4:09 pm

You should teach my boyfriend a few things. He thinks that us playing XBox games together is romantic. By the way, we’re both over 30! Go figure!
I will make some of these suggestions to him. Hell, I’ll just send him the link to your blog via email! Great suggestions! :)

40 Spense December 7, 2010 at 5:57 pm

Snowball fights are one of my favorites.

It’s childlike fun that can turn into a romantic time.
We tried it at the beach once, but substituting the snow for sand somehow just made my wife angry.

Go figure.

41 Tryclyde December 7, 2010 at 6:59 pm

As a couple of people have said, Christmas Vacation needs to be in the top three of any list of Christmas movies…..My wife also loves drinking spiked eggnog that I make from scratch every Christmas Eve….Also, if you’re near the NY Metropolitan area, Central Park during the Christmas season is awesome (Rockefeller Center is way too crowded and touristy), and you can get good-priced tickets to the Radio City Christmas Spectacular – fantastic show.

42 Matt December 7, 2010 at 7:06 pm

Great ideas!

Another volunteering idea would be to go in on an Angel Tree child together and spend an afternoon buying the items for that child. I agree that this should probably be done after having been with someone for a while (especially when trying to decide how much money each will contribute).

Would you mind sharing where you got the image for the Christmas Movie Night? I could really use it for a holiday project I’m working on.

43 Erasmus December 7, 2010 at 7:34 pm

@Bill: You’re an idiot if you are incapable of recognizing the manly acknowledgment of our wives in the time honored “wink, wink, nudge, nudge.”

Which reminds me Brett, congratulations once again on the beginning of your own dynasty, little Gus.

44 J.D. December 7, 2010 at 10:32 pm

My wife and I began looking for a Christmas movie to turn into a yearly tradition. A few years ago we found a foreign film, “Joyeaux Noel”. It is set on Christmas Eve, in the trenches of WW1. Along with the standard line-up of films, it has become a favorite.

45 Josh December 8, 2010 at 1:54 am

Great post, the movie night is always a good one with the girlfriend. You guys must have forgotten that “Gremlins” is also a Christmas movie. Other favorites are also:

Home Alone
Muppets Christmas Carol (don’t hate, I’ve been watching it since I was a kid)

Thanks for the other suggestions gents! Merry Christmas!

46 Tom December 8, 2010 at 1:25 pm

Ok call me old fashioned but what about building a snow man then having a romantic snow ball fight. Think of the junior high days and let your mind go wild then after your both wet and cold build a roaring fire and for safety reasons warm each others bodies. This can be done a number of ways but in all my emergency classes the first thing is to remove wet clothes remember safety first.

47 Carter December 10, 2010 at 11:11 am

This is definitely not in the inexpensive category, but I just got back from New York with my girlfriend, now fiance, and the city looks great at Christmas!

Baking and decorating cookies and watching Christmas movies have been successes for me!

48 Danny Verpoort December 13, 2010 at 5:11 pm

Ok so I got this date coming up with my girl. What I’ve got planned: a stroll trough the snow (?), backing cookies with her and then watch a christmas film whilst stuffing ourselfs with cookies. Any other ideas? I’ll be sure to let you know how it went :)

49 Will December 13, 2010 at 10:19 pm

@Brett – Thanks!

50 AlaskaMinxy December 16, 2010 at 4:29 pm

What about Chevy Chases’ Christmas Vacation?! For those of us with idiot families, this is a perfect stress reliever!

51 Victory Unlimited December 17, 2010 at 12:31 am

This was a very good post.

What I like about it specifically is that the choices of date ideas that Brett gives tend to be well-balanced. What I mean by that is that they are a mixture of “action dates”, “quiet dates”, and even “group-type dates”. What all these suggestions have in common is that they are all centered around an event that can be used to BOND a couple even closer together than they were BEFORE they go on these dates.

All of these factors lend themselves to making MANY great memories that can be used in the years to come to spark our imaginations, and to stir up some real passion between couples just by thinking back on “what we did Holiday Season of last year”.

We all know that holidays and other special days that hold sentimental value to us are EXCELLENT times to build more closeness between us and our significant others——our wives and our girlfriends too.

On that note, I had been getting quite a few requests from a lot of single and lonely guys as to what they could do to actually find someone before the holiday season was over. So I posted a show a few days ago on my website that lists the Top Ten strategies guys can use to find a girl BEFORE the holidays are over. In a way,

I guess you could think of it as a preliminary list that compliments the list that Brett has compiled. On the show, I go over each strategy in-depth because I think a lot of people who HAVE someone for the holidays tend to forget what it feels like to be a guy sitting at home alone.

Well, I haven’t forgotten. And I’d encourage everybody here to reach out to some of their single guy friends over these holidays to make sure that they know that YOU definitely haven’t forgotten them either.

PEACE to everyone here.

Victory Unlimited

52 Shelley Bell December 17, 2010 at 2:17 am

Haha this is awesome!!!

53 Lena December 20, 2010 at 10:16 pm

The Shop Around the Corner is an awesome holiday movie. It has Jimmy Stewart and Margaret Sullivan.


“You’ve Got Mail” is a not so great adaptation. I prefer the original.

54 Beth December 27, 2010 at 12:44 pm

So, as a single gal let me just tell you that I love this list…. Christmas lights is a great date idea as is the volunteering. I like that several of the ideas are inexpensive. To all the men………..Step up and invite your wife, girlfriend, or a woman that you would like to have as your girlfriend….. She will appreciate it..

55 Jon December 28, 2010 at 11:55 am

Another great movie to add to the list: “Christmas in Connecticut,” with the incomparable Barbara Stanwyck and Sydney Greenstreet. http://www.imdb.com/title/tt0037595/ An absolute classic romantic comedy, the kind that real men canenjoy.

56 Evan December 30, 2010 at 10:27 pm

Good stuff, gota love AoM!!

57 Saisyuu December 6, 2012 at 7:56 am

Great list. A lot of cities have Christmas markets set up in some form. Under the lighting of the city’s artificial lighting and the dim moon, it can create a really good atmosphere. Nice holiday spirit, not to mention an excuse to go check out and purchase stuff you maybe usually wouldn’t be able to.

58 Trevor Meyer December 10, 2012 at 3:50 pm

Thanks for posting this! I’m sort of striking up a relationship at the moment, and I think the Christmas Light idea would be a fantastic date (anyone familiar with The Mission Inn in Riverside, CA knows what I’m talkin about).

59 Jared W December 10, 2012 at 9:31 pm

Lest you forget “Christmas in Connecticut”, for a lesser known Christmas Classic, circa WWII.

60 Hippy Gal December 10, 2013 at 9:04 pm

Just wanted to say thank you

61 Charles January 10, 2014 at 4:04 pm

For the quirky, The Nightmare Before Christmas is another holiday flick with a romantic theme running throughout.

My dearest friend, if you don’t mind I’d like to join you by your side where we can gaze into the stars and sit together now and forever for it is plain as anyone can see we’re simply meant to be. Sally and Jack Skellington

Leave a Comment

Previous post:

Next post:

Site Meter